Record Information |
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Version | 1.0 |
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Created at | 2022-09-09 17:43:46 UTC |
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Updated at | 2022-09-09 17:43:46 UTC |
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NP-MRD ID | NP0288143 |
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Secondary Accession Numbers | None |
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Natural Product Identification |
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Common Name | (2r)-2-[(1r,2r,3ar,5ar,9as,11ar)-2-hydroxy-3a,6,6,9a,11a-pentamethyl-7-oxo-1h,2h,3h,4h,5h,5ah,8h,9h,10h,11h-cyclopenta[a]phenanthren-1-yl]-6-methyl-5-methylideneheptanoic acid |
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Description | 16Alpha-hydroxyeburiconic acid, also known as 16α-hydroxyeburiconate, belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units. (2r)-2-[(1r,2r,3ar,5ar,9as,11ar)-2-hydroxy-3a,6,6,9a,11a-pentamethyl-7-oxo-1h,2h,3h,4h,5h,5ah,8h,9h,10h,11h-cyclopenta[a]phenanthren-1-yl]-6-methyl-5-methylideneheptanoic acid is found in Daedalea dickinsii, Daedalea quercina and Fomitopsis pinicola. It was first documented in 2022 (PMID: 36113962). Based on a literature review a significant number of articles have been published on 16alpha-hydroxyeburiconic acid (PMID: 36113854) (PMID: 36113832) (PMID: 36113821) (PMID: 36113819). |
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Structure | CC(C)C(=C)CC[C@H]([C@H]1[C@H](O)C[C@@]2(C)C3=C(CC[C@]12C)[C@@]1(C)CCC(=O)C(C)(C)[C@@H]1CC3)C(O)=O InChI=1S/C31H48O4/c1-18(2)19(3)9-10-20(27(34)35)26-23(32)17-31(8)22-11-12-24-28(4,5)25(33)14-15-29(24,6)21(22)13-16-30(26,31)7/h18,20,23-24,26,32H,3,9-17H2,1-2,4-8H3,(H,34,35)/t20-,23-,24+,26+,29-,30-,31+/m1/s1 |
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Synonyms | Value | Source |
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16a-Hydroxyeburiconate | Generator | 16a-Hydroxyeburiconic acid | Generator | 16alpha-Hydroxyeburiconate | Generator | 16Α-hydroxyeburiconate | Generator | 16Α-hydroxyeburiconic acid | Generator |
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Chemical Formula | C31H48O4 |
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Average Mass | 484.7210 Da |
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Monoisotopic Mass | 484.35526 Da |
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IUPAC Name | (2R)-2-[(2S,7R,11R,13R,14R,15R)-13-hydroxy-2,6,6,11,15-pentamethyl-5-oxotetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-1(10)-en-14-yl]-6-methyl-5-methylideneheptanoic acid |
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Traditional Name | (2R)-2-[(2S,7R,11R,13R,14R,15R)-13-hydroxy-2,6,6,11,15-pentamethyl-5-oxotetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-1(10)-en-14-yl]-6-methyl-5-methylideneheptanoic acid |
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CAS Registry Number | Not Available |
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SMILES | CC(C)C(=C)CC[C@H]([C@H]1[C@H](O)C[C@@]2(C)C3=C(CC[C@]12C)[C@@]1(C)CCC(=O)C(C)(C)[C@@H]1CC3)C(O)=O |
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InChI Identifier | InChI=1S/C31H48O4/c1-18(2)19(3)9-10-20(27(34)35)26-23(32)17-31(8)22-11-12-24-28(4,5)25(33)14-15-29(24,6)21(22)13-16-30(26,31)7/h18,20,23-24,26,32H,3,9-17H2,1-2,4-8H3,(H,34,35)/t20-,23-,24+,26+,29-,30-,31+/m1/s1 |
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InChI Key | MUTPNNQAZRJDSK-WMNQUVFJSA-N |
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Experimental Spectra |
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| Not Available | Predicted Spectra |
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| Spectrum Type | Description | Depositor ID | Depositor Organization | Depositor | Deposition Date | View |
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1D NMR | 13C NMR Spectrum (1D, 25 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 100 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 252 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 1000 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 50 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 200 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 75 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 300 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 101 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 400 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 126 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 500 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 151 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 600 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 176 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 700 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 201 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 800 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 226 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 900 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum |
| Chemical Shift Submissions |
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| Not Available | Species |
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Species of Origin | |
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Chemical Taxonomy |
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Description | Belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units. |
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Kingdom | Organic compounds |
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Super Class | Lipids and lipid-like molecules |
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Class | Prenol lipids |
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Sub Class | Triterpenoids |
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Direct Parent | Triterpenoids |
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Alternative Parents | |
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Substituents | - Triterpenoid
- Hydroxy bile acid, alcohol, or derivatives
- Monohydroxy bile acid, alcohol, or derivatives
- Bile acid, alcohol, or derivatives
- Steroid acid
- Hydroxysteroid
- 3-oxosteroid
- 3-oxo-5-alpha-steroid
- 16-hydroxysteroid
- 16-alpha-hydroxysteroid
- 14-alpha-methylsteroid
- Oxosteroid
- Steroid
- Medium-chain fatty acid
- Hydroxy fatty acid
- Fatty acyl
- Fatty acid
- Unsaturated fatty acid
- Cyclic alcohol
- Ketone
- Cyclic ketone
- Secondary alcohol
- Monocarboxylic acid or derivatives
- Carboxylic acid
- Carboxylic acid derivative
- Alcohol
- Organic oxide
- Carbonyl group
- Organic oxygen compound
- Organooxygen compound
- Hydrocarbon derivative
- Aliphatic homopolycyclic compound
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Molecular Framework | Aliphatic homopolycyclic compounds |
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External Descriptors | Not Available |
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Physical Properties |
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State | Not Available |
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Experimental Properties | Property | Value | Reference |
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Melting Point | Not Available | Not Available | Boiling Point | Not Available | Not Available | Water Solubility | Not Available | Not Available | LogP | Not Available | Not Available |
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Predicted Properties | |
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General References | - Truchetet ME, Drumez E, Barnetche T, Martin C, Devaux M, Goulenok T, Maria A, Schmidt J, Abdallah NA, Melki I, Hachulla E, Richez C: Outcome of COVID-19 in patients with rheumatic and inflammatory diseases treated with mycophenolic acid: data from the French RMD COVID-19 cohort. RMD Open. 2022 Sep;8(2). pii: rmdopen-2022-002476. doi: 10.1136/rmdopen-2022-002476. [PubMed:36113962 ]
- Tong KP, Intine R, Wu S: Vitamin C and the management of diabetic foot ulcers: a literature review. J Wound Care. 2022 Sep 1;31(Sup9):S33-S44. doi: 10.12968/jowc.2022.31.Sup9.S33. [PubMed:36113854 ]
- Traczyk G, Swiatkowska A, Hromada-Judycka A, Janikiewicz J, Kwiatkowska K: An intact zinc finger motif of the C1B domain is critical for stability and activity of diacylglycerol kinase-epsilon. Int J Biochem Cell Biol. 2022 Sep 13;152:106295. doi: 10.1016/j.biocel.2022.106295. [PubMed:36113832 ]
- Cai Y, Zhai L, Wu K, Li Z, Gu Z, Wang Y, Cui X, Zhou T, Ruan R, Liu T, Liu Y, Zhang Q: Mechanisms of promotion in the heterotrophic growth of Chlorella vulgaris by the combination of sodium acetate and hydrolysate of broken rice. Bioresour Technol. 2022 Sep 14;364:127965. doi: 10.1016/j.biortech.2022.127965. [PubMed:36113821 ]
- Sun J, Wang G, Liu H, Zhang Y, Sun H, Dai X: Influence of thermally activated peroxodisulfate pretreatment on gaseous emission, dissolved organic matter and maturity evolution during spiramycin fermentation residue composting. Bioresour Technol. 2022 Nov;363:127964. doi: 10.1016/j.biortech.2022.127964. Epub 2022 Sep 13. [PubMed:36113819 ]
- LOTUS database [Link]
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